EP1575904B2 - Procede de fabrication en continu d'isocyanates - Google Patents
Procede de fabrication en continu d'isocyanates Download PDFInfo
- Publication number
- EP1575904B2 EP1575904B2 EP03789262.7A EP03789262A EP1575904B2 EP 1575904 B2 EP1575904 B2 EP 1575904B2 EP 03789262 A EP03789262 A EP 03789262A EP 1575904 B2 EP1575904 B2 EP 1575904B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- stage
- phosgene
- reaction
- pressure
- reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 78
- 239000012948 isocyanate Substances 0.000 title description 96
- 150000002513 isocyanates Chemical class 0.000 title description 88
- 238000010924 continuous production Methods 0.000 title description 21
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 204
- 238000006243 chemical reaction Methods 0.000 claims abstract description 161
- 150000001412 amines Chemical class 0.000 claims abstract description 85
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 13
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 33
- 239000007791 liquid phase Substances 0.000 claims description 26
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 20
- 239000012442 inert solvent Substances 0.000 claims description 20
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 9
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 6
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 238000011144 upstream manufacturing Methods 0.000 claims 2
- 238000002156 mixing Methods 0.000 abstract description 49
- 238000000926 separation method Methods 0.000 abstract description 20
- 239000002904 solvent Substances 0.000 description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
- -1 aliphatic isocyanates Chemical class 0.000 description 57
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 53
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 49
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 21
- 239000007789 gas Substances 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000006227 byproduct Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 11
- 150000003141 primary amines Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 201000006747 infectious mononucleosis Diseases 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 150000003672 ureas Chemical class 0.000 description 5
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010010774 Constipation Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KAFSRAJLBOFODY-UHFFFAOYSA-N carbonyl dichloride chlorobenzene Chemical compound ClC1=CC=CC=C1.C(=O)(Cl)Cl KAFSRAJLBOFODY-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000009790 rate-determining step (RDS) Methods 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000021715 photosynthesis, light harvesting Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
Claims (12)
- Procédé de fabrication de polyisocyanates par réaction d'amines organiques avec du phosgène dans un solvant inerte, caractérisé en ce que la réaction a lieu en au moins trois étapes, la première étape étant réalisée dans une buse, la deuxième étape dans au moins un appareil à temps de séjour et la troisième étape dans une ou plusieurs colonnes de réaction, et la pression dans chaque étape ultérieure étant inférieure à celle de l'étape précédente,- la pression avant la buse de la première étape étant de 3 à 70 bar, dans l'appareil à temps de séjour de la deuxième étape de 2,5 à 35 bar et dans la colonne de réaction de la troisième étape de 2 à 20 bar,- la séparation du phosgène en excès ayant lieu dans la colonne de réaction ou à une étape ultérieure et- la température au fond de la colonne de réaction étant de 80 à 190°C et à la tête de la colonne de réaction de 50 à 120°C.
- Procédé selon la revendication 1, caractérisé en ce que les polyisocyanates sont le diisocyanate de diphénylméthane (MDI), le polyisocyanate de polyphénylène-polyméthylène (PMDI) ou des mélanges de ces deux composés, le diisocyanate de toluylène (TDI), le diisocyanate d'hexaméthylène (HDI) ou le diisocyanate d'isophorone (IPDI).
- Procédé selon la revendication 1, caractérisé en ce qu'un réacteur tubulaire, une cuve agitée, un appareil à temps de séjour non agité ou un appareil de séparation de phases pour phase vapeur et phase liquide est utilisé en tant qu'appareil pour la deuxième étape.
- Procédé selon les revendications 1 à 3, caractérisé en ce que temps de séjour dans l'appareil à temps de séjour de la deuxième étape est de 1 seconde à 30 minutes, de préférence de 30 secondes à 10 minutes, de manière particulièrement préférée de 2 à 7 minutes.
- Procédé selon les revendications 1 à 4, caractérisé en ce que le réacteur à temps de séjour de la deuxième étape est réalisé par deux réacteurs ou plus identiques ou différents, qui sont connectés en parallèle ou en série.
- Procédé selon la revendication 1, caractérisé en ce que la séparation du phosgène est réalisée dans l'appareil de la troisième étape, la colonne de réaction.
- Procédé selon la revendication 1, caractérisé en ce que la pression du réacteur de la première étape est réduite à la pression du réacteur de la deuxième étape par une vanne de régulation ou un autre dispositif caractérisé par une perte de charge.
- Procédé selon la revendication 1, caractérisé en ce que la pression du réacteur de la deuxième étape est réduite à la pression du réacteur de la troisième étape par une vanne de régulation ou un autre dispositif caractérisé par une perte de charge.
- Procédé selon la revendication 1, caractérisé en ce que le réacteur de la première étape est intégré dans le réacteur de la deuxième étape.
- Procédé selon les revendications 1 à 8, caractérisé en ce que la pression avant la buse de la première étape est de 15 à 45 bar, la pression dans le réacteur à temps de séjour de la deuxième étape est de 15 à 35 bar, et la pression dans la colonne de réaction de la troisième étape est de 3,5 à 16 bar.
- Procédé selon les revendications 1 à 9, caractérisé en ce que la température dans la première, deuxième et troisième étape est à chaque fois de 80 à 190°C, de préférence de 90 à 150°C.
- Procédé selon les revendications 1 à 10, caractérisé en ce qu'un hydrocarbure aromatique, tel que le toluène, ou de préférence un hydrocarbure aromatique chloré, tel que le chlorobenzène, l'ortho-dichlorobenzène ou le trichlorobenzène ou leurs mélanges, est utilisé en tant que solvant inerte.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10260082A DE10260082A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
| DE10260082 | 2002-12-19 | ||
| PCT/EP2003/014185 WO2004056756A1 (fr) | 2002-12-19 | 2003-12-13 | Procede de fabrication en continu d'isocyanates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP1575904A1 EP1575904A1 (fr) | 2005-09-21 |
| EP1575904B1 EP1575904B1 (fr) | 2010-10-13 |
| EP1575904B2 true EP1575904B2 (fr) | 2013-09-04 |
Family
ID=32404069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03789262.7A Expired - Lifetime EP1575904B2 (fr) | 2002-12-19 | 2003-12-13 | Procede de fabrication en continu d'isocyanates |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7851648B2 (fr) |
| EP (1) | EP1575904B2 (fr) |
| JP (1) | JP4324558B2 (fr) |
| KR (1) | KR101032936B1 (fr) |
| CN (1) | CN1312123C (fr) |
| AT (1) | ATE484492T1 (fr) |
| AU (1) | AU2003293871A1 (fr) |
| DE (2) | DE10260082A1 (fr) |
| ES (1) | ES2353005T5 (fr) |
| MX (1) | MXPA05006058A (fr) |
| PT (1) | PT1575904E (fr) |
| WO (1) | WO2004056756A1 (fr) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004032871A1 (de) * | 2004-07-07 | 2006-02-09 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyisocyanaten durch adiabate Phosgenierung von primären Aminen |
| ATE412463T1 (de) | 2005-04-08 | 2008-11-15 | Huntsman Int Llc | Spiralmischerdüse und verfahren zum mischen von zwei oder mehr fluiden und verfahren zur herstellung von isocyanaten |
| MX2007014890A (es) * | 2005-05-30 | 2008-01-28 | Huntsman Int Llc | Proceso para la preparacion de poliisocianatos de la serie de difenilmetano. |
| DE102005043799A1 (de) * | 2005-09-13 | 2007-04-12 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| CN100339363C (zh) * | 2006-05-08 | 2007-09-26 | 江苏安邦电化有限公司 | 一种丁基异氰酸酯的制备方法 |
| DE102006022448A1 (de) * | 2006-05-13 | 2007-11-15 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
| US7547801B2 (en) * | 2006-06-26 | 2009-06-16 | Bayer Materialscience Llc | Process for the continuous preparation of isocyanates |
| ES2476248T3 (es) * | 2006-10-26 | 2014-07-14 | Basf Se | Procedimiento para la preparación de isocianatos |
| HUE029625T2 (en) * | 2006-11-07 | 2017-03-28 | Basf Se | Process for the preparation of isocyanates |
| JP2010512364A (ja) * | 2006-12-11 | 2010-04-22 | ビーエーエスエフ ソシエタス・ヨーロピア | イソシアネートの製造法 |
| HUE027861T2 (en) * | 2007-11-14 | 2016-11-28 | Covestro Deutschland Ag | Preparation of pale isocyanates |
| DE102007061688A1 (de) | 2007-12-19 | 2009-06-25 | Bayer Materialscience Ag | Verfahren und Mischaggregat zur Herstellung von Isocyanaten durch Phosgenierung primärer Amine |
| DE102008012037A1 (de) | 2008-03-01 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Methylen-diphenyl-diisocyanaten |
| DE102008000785A1 (de) * | 2008-03-20 | 2009-09-24 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
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| US9321720B2 (en) | 2010-10-14 | 2016-04-26 | Basf Se | Process for preparing isocyanates |
| EP2627629B1 (fr) * | 2010-10-14 | 2021-12-08 | Basf Se | Procédé de production d'isocyanates |
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| JP2014520086A (ja) | 2011-05-24 | 2014-08-21 | ビーエーエスエフ ソシエタス・ヨーロピア | バイオマスからポリイソシアナートを製造する方法 |
| EP2559658A1 (fr) * | 2011-08-19 | 2013-02-20 | Huntsman International LLC | Procédé de séparation de chlorure de carbonyle et de chlorure d'hydrogène d'un flux fluide comportant du chlorure de carbonyle et du chlorure d'hydrogène |
| CN103764626A (zh) * | 2011-09-02 | 2014-04-30 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| CN108147980B (zh) | 2012-09-24 | 2020-10-23 | 科思创德国股份有限公司 | 通过二胺悬浮体的光气化制备二异氰酸酯的方法 |
| BR112015008481A2 (pt) | 2012-10-24 | 2017-07-04 | Basf Se | processo para a preparação de isocianatos pela reação de aminas com fosgênio na fase líquida. |
| US9126904B2 (en) | 2012-10-24 | 2015-09-08 | Basf Se | Process for preparing isocyanates by phosgenation of amines in the liquid phase |
| CN103214397B (zh) * | 2013-04-15 | 2015-02-25 | 湘潭大学 | 连续制备1,5-萘二异氰酸酯的方法 |
| WO2015144682A1 (fr) * | 2014-03-27 | 2015-10-01 | Bayer Material Science Ag | Procédé pour faire fonctionner une installation de phosgénation en phase gazeuse |
| KR20160137545A (ko) * | 2014-03-27 | 2016-11-30 | 코베스트로 도이칠란트 아게 | 이소시아네이트의 제조 방법 |
| PT3134384T (pt) * | 2014-04-23 | 2019-01-29 | Basf Se | Processo para a produção de isocianatos em carbonatos de dialquilo como solvente |
| JP2017527596A (ja) * | 2014-09-19 | 2017-09-21 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | 気相中でイソシアネートを製造するための方法 |
| CN104356028B (zh) * | 2014-09-29 | 2017-10-20 | 湖南海利常德农药化工有限公司 | 一种连续化生产制备3,4二氯苯基异氰酸酯的方法 |
| US10815193B2 (en) | 2015-06-29 | 2020-10-27 | Covestro Deutschland Ag | Process for providing hydrogen chloride for chemical reactions |
| KR20180022843A (ko) | 2015-06-29 | 2018-03-06 | 코베스트로 도이칠란트 아게 | 폴리이소시아네이트를 제조하는 방법 |
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| US10875827B2 (en) * | 2018-11-13 | 2020-12-29 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatic phosgenation of the corresponding amine |
| EP4077274A1 (fr) | 2019-12-18 | 2022-10-26 | Covestro Deutschland AG | Procédé de production de diisocyanates et de polyisocyanates de la série du diphénylméthane |
| CN116034102A (zh) | 2020-09-01 | 2023-04-28 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| WO2022147830A1 (fr) * | 2021-01-11 | 2022-07-14 | 万华化学集团股份有限公司 | Procédé de préparation d'un polyisocyanate et dispositif de réaction associé |
| CN113666844A (zh) * | 2021-09-22 | 2021-11-19 | 德州绿霸精细化工有限公司 | 一种连续生产2,6-二氟苯甲酰基异氰酸酯的方法 |
| CN114685315B (zh) * | 2022-05-09 | 2023-07-21 | 山东新和成精化科技有限公司 | 一种异氰酸酯的制备方法及装置 |
| CN114920668B (zh) * | 2022-05-13 | 2023-10-13 | 万华化学集团股份有限公司 | 一种制备低氯代杂质异氰酸酯的方法 |
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-
2002
- 2002-12-19 DE DE10260082A patent/DE10260082A1/de not_active Withdrawn
-
2003
- 2003-12-13 EP EP03789262.7A patent/EP1575904B2/fr not_active Expired - Lifetime
- 2003-12-13 DE DE50313194T patent/DE50313194D1/de not_active Expired - Lifetime
- 2003-12-13 AT AT03789262T patent/ATE484492T1/de not_active IP Right Cessation
- 2003-12-13 KR KR1020057011319A patent/KR101032936B1/ko active IP Right Grant
- 2003-12-13 ES ES03789262.7T patent/ES2353005T5/es not_active Expired - Lifetime
- 2003-12-13 WO PCT/EP2003/014185 patent/WO2004056756A1/fr active Application Filing
- 2003-12-13 MX MXPA05006058A patent/MXPA05006058A/es active IP Right Grant
- 2003-12-13 US US10/539,802 patent/US7851648B2/en active Active
- 2003-12-13 JP JP2004561288A patent/JP4324558B2/ja not_active Expired - Fee Related
- 2003-12-13 AU AU2003293871A patent/AU2003293871A1/en not_active Abandoned
- 2003-12-13 CN CNB2003801068020A patent/CN1312123C/zh not_active Expired - Lifetime
- 2003-12-13 PT PT03789262T patent/PT1575904E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2353005T3 (es) | 2011-02-24 |
| CN1312123C (zh) | 2007-04-25 |
| JP2006510692A (ja) | 2006-03-30 |
| KR101032936B1 (ko) | 2011-05-06 |
| WO2004056756A1 (fr) | 2004-07-08 |
| JP4324558B2 (ja) | 2009-09-02 |
| PT1575904E (pt) | 2010-11-09 |
| AU2003293871A1 (en) | 2004-07-14 |
| US7851648B2 (en) | 2010-12-14 |
| DE10260082A1 (de) | 2004-07-01 |
| ES2353005T5 (es) | 2014-01-09 |
| MXPA05006058A (es) | 2005-08-16 |
| CN1729168A (zh) | 2006-02-01 |
| KR20050089055A (ko) | 2005-09-07 |
| US20060252960A1 (en) | 2006-11-09 |
| ATE484492T1 (de) | 2010-10-15 |
| DE50313194D1 (de) | 2010-11-25 |
| EP1575904A1 (fr) | 2005-09-21 |
| EP1575904B1 (fr) | 2010-10-13 |
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